Long time reader, first time poster. I’d love the community’s feedback on this.

I like one of my friends. Known her for two years, and while we’re technically coworkers, we’re in two different departments. I’ve resisted asking anyone at work out ever since a debacle nearly 9 years ago, but I feel that was different since the woman I liked then was one of my supervisors. This new woman - we’re in related departments, but she isn’t on my actual team.

I know we’re actual friends, I’m not just in the friendzone. In my experience, when I’ve been in the friendzone, it’s always been lip service from the female. We have the talk, I end pursuit amicably, but then afterward it’s always been me trying to maintain contact 100%. Of course I don’t keep following those women around for very long, but I’m just illustrating what I’m sure is the sad friendzone experience. It’s frustrating, but in the end acceptable since most people with self-respect are able to move on pretty quickly.

With my current friend and interest, we truly enjoy hanging out. It started when I got to know her through work, and then after a few months invited her to a bar & karaoke night with other friends. Ever since then, we’ve hung out alone many times, with other groups, over weekends & holidays, and it always feels natural. Our personalities just….mesh. Like, because I’m comfortable I feel like I’ve been able to be charming by default. There have never been any awkward silences whenever we’ve been together.

Yesterday was the most recent example of this. We spent like 4+ hours together. I just got back from a trip to Japan, and we had a picnic in the park. I told her about the amazing time I had, showed her some trip pics, and gave her a small souvenir. She did the same for me a few months ago when she came back from a trip to Korea. All of this mixed with some pretty deep conversations. We felt we needed to get up & move after about two hours in the sun, but things continued over a long walk for another couple hours. All throughout the picnic and walk, the touch barrier was broken. I’d put a hand on a knee, over her shoulder, graze her hand / she’d put a hand over my shoulder, graze my hand, and give light play shoves after a wisecrack. I also was fully intent on listening to her and maintaining healthy eye contact (hence the rich conversations we always have).

It does need to be stated that she calls me “buddy” and “bro.” While that could be the kiss of death for anything more than friendship, I do see other possible interpretations such as women using those words to communicate with those they're truly close with. In any case, I’m not using those two words as a signal to back off yet.

It’s only been a few months since I became attracted to her and have wanted more than a friendship. I’ve resisted doing anything not so much because of work, but because I don’t want to destroy the rich friendship we already have should she not feel the same way. Yesterday’s wonderful 4 hours were the first time I’d been with her alone and was able to begin escalating (through touching, eye contact, jokes, & the occasional compliment). She’s leaving for another trip to Korea in two weeks, but we’ve already got a desire to do a movie night over at my place (her idea) when she gets back. We’re both into Sci-Fi and I believe I got her intrigued with the idea of Star Trek: Strange New Worlds. She also likes a ton of classic anime I watched back in college like Fullmetal Alchemist and Ranma 1/2 (we’ve both not really kept up with newer stuff).

I want to make a move soon. She did mention she was quarantining before her next trip, so I’ll realistically be seeing her in-person again next about a month from now. If you’ve read this long spiel up to this point, thank you. I’m wondering when to just grow a pair and ask her out. My gut tells me that the friendship wouldn’t be destroyed if she said no, and I can’t do nothing. Would you all try hinting/escalating more before asking? Simply that I’d like to take her on a real date.